


Roll a Dexterity Check

by GlitterDwarf



Category: Silicon Valley (TV)
Genre: M/M, Post-Episode: s02e05
Language: English
Status: Completed
Published: 2015-05-19
Updated: 2015-05-29
Packaged: 2018-03-31 06:55:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,668
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3968650
Author URL: https://archiveofourown.org/users/GlitterDwarf/pseuds/GlitterDwarf
Summary: <blockquote class="userstuff">
              <p>"Fortunately, our wonderful CEO Richard Hendricks graciously allowed me to sleep on a cot in his room. I felt so tiny and safe in that womb of innovation that I cannot describe the feeling." -Jared in the PiedPiper.com blog</p><p>Richard's Paladin was in need, and as a good DM he needed to help.</p><p>Post-episode S02E05: Server Space.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I actually am writing multiple things and wanted this done before Episode 6, but I failed completely. So here is the first half, conveniently cut before porn happens for those who aren't interested in that sort of thing.
> 
> (Also, full disclosure, whenever I did table-top RPGs it was with a custom system, so I could be 10000000% bastardizing the actual D&D rules.)

In his teen years (and, let’s be honest, pretty far into his foray at University) Richard played a lot of D&D, to the surprise of no one at all. It was a nice, short-lived escape to play through a few campaigns in his spare time. Naturally that free time had become non-existent after getting hired by Hooli, and not even the lure of there being three girls in Hooli's in-house D&D team was enough to lure him back into gaming.

You can never really leave completely, though, he found. Not that he would say it out loud, but in his mind, when the house was relatively quiet and he was falling asleep, he would visualize himself as the Dungeon Master of Pied Piper and in control of the story. It was strangely empowering, this exercise, and he was sure that Jared would be able to tell him which corporate strategy it was most like (as sure as he was that Jared would be the only one who wouldn't ruin the practice for him with ridicule). It helped a lot when it seemed like every day brought new challenges to his business, new and exciting ways to fuck everything up. He had at least a little room to breathe at night and reimagine the day as a series of stories to tell and problems to solve. Hooli became a rival band of fighters seeking the same treasures, Russ became a mysterious and reckless–but rich–Aristocrat (maybe a former Rogue with entrepreneurial instincts?), and most recently the asshole neighbor could be the warm-up Troll to get rid of for quick character points.

And so, armed with knowledge, he completely nuked that Troll with help from Erlich (the Narcissistic Fighter). With no more immediate enemies to slay, Richard returned to his room.

To be met with erratic, frightening-sounding German.

Richard sighed and stood just inside the doorway, considering. There really was no place to sleep outside his room, and he wouldn't want to deal with getting fucked with if anyone found that he was soaked any furniture with his sweat. There was no way, though, that he could sleep with Jared like this.

He frowned and sighed. The choice was easy; his Paladin was in need, and as a good DM he needed to help.

Richard knelt down and slowly shuffled forward until his knees met the edge of the thin, old and mostly-deflated air mattress Jared was using. With a shaky hand he reached out and gently, awkwardly pressed against Jared's shoulder enough to shift his body. There was a short pause, but no real change. Carefully, Richard pushed against Jared’s shoulder again, harder this time. This did the trick which, of course, backfired; the other man twitched and started fighting with the air, hands erratically swinging. Richard made a (completely dignified) gurgling noise and reached out to grip Jared's hands by the wrists, worried that he would hurt himself. To his surprise Jared calmed, and the German became a quiet whisper. Curiously, he pressed his thumbs harder into the inside of Jared's wrists and tightened his grip, eliciting a soft moan. Richard suppressed a shiver; the implications–and the memory of every time Jared mentioned liking when Richard was assertive and looked at him with dark eyes–brought to mind some vivid imagery, but this was no time to get worked up sexuality when he was just trying to help.

Gently, Richard lowered both of their arms until Jared's were at his side and let go. Jared immediately frowned, grabbed at Richard’s hands with surprising strength and started talking in his sleep again.

Richard sighed as he struggled against gravity in his current, awkward position, somewhat between kneeling and being pulled onto Jared’s chest. He needed to sleep, Jared needed to be quiet, and in the morning he could come up with an explanation that his exhausted brain failed to find in the moment. Carefully maneuvering around Jared’s grip he shrugged the kimono off, crawled under Jared's blanket, and arranged the two of them into a spooning position.

As he drifted asleep he thought that the silence was beautiful and sent a hope into the universe that Jared not freak out when he woke up and found himself not only groped inappropriately but also covered in Richard's inevitable sweat. His final thoughts that night (morning?) were drafting the help wanted ad for a Business Development Head With Additional Therapeutic Needs TBD.

 

* * *

 

The morning light woke Richard. There was a single beam that happened after an errant cloud moved in the sky, shooting a stream of light through the one broken slat in the blinds and directly into Richard’s eyes. He groaned as he was startled awake, confused after forgetting for a moment why the _fuck_ he was on the ground.

Then soft, sweet-smelling hair reminded him.

At some point during the night they had become entangled. Jared had turned and was currently curled into Richard's chest. He was essentially fucking cradling the other man in his arms, with one hand curled around Jared's hip and the other in Jared's hair. It was funny, holding somebody taller than yourself, but Richard found that they Tetris’d together surprisingly well for two men that were so awkward and uncoordinated in their waking lives.

He stayed silent for a few moments to listen to Jared's breaking. It was even but audible, a good sign that he was still asleep. Richard quickly ran through the scenarios of figuring out the way to extricate himself as quickly as possible, but he also decided that the temptation to do something–just a quick touch, to live the fantasy for even a moment–was too strong. He lightly carded his fingers through Jared's hair and kissed the top of his head.

That surprised noise that followed was unmistakable; Jared was awake.

A beat of silence, and then they both gasped out "sorry!"

Another beat of silence, then a simultaneous "it's okay!"

Jared huffed out a surprised laugh (and Richard fought very hard to not make an embarrassing noise at the feeling of Jared's hot breath against his neck) and then said, slowly, "Richard, I have several questions."

"Uh," Richard responded intelligently, "well. You were having what I think are night terrors? There was this German yelling and I don’t know, I thought it might be like snoring where if you just, uh, move the body they might stop? But it didn’t, but when I touched you–not like that! That didn’t come out right–well it, uh, it calmed you down? I'm sorry if this is too creepy."

"Oh," Jared breathed. "That is...incredibly kind of you. I'm sorry to have been an inconvenience."

"No, Jared, it's okay. As long as you're okay. Are you okay?"

"Oh, yes."

Richard kept his body as still as possible. Neither had started to move, but Jared probably just didn't want to be impolite. That was kind of his thing, laying face-down in the mud just to make sure nobody else’s shoes got dirty.

But then Jared moved one of his hands. One was curled below his own head, somewhere between Richard’s chest and ribs, but the other was now lightly scratching at his back.

"Richard, you didn't sweat."

"Oh! Cool," he replied. It was true; for the first time in over a week he awoke dry and fucking normal.

They had still not moved to disentangle themselves.

"I also cannot hear any distressing noises from your stomach, which happens sometimes in the morning for you.” Richard blinked a few times in confusion, but this was a passing emotion compared to the way his body was reacting to the gentle scratches. Jared’s next words were spoken slowly, in that way that he spoke when he wanted to make sure Richard stayed calm. “I don’t want to make you uncomfortable but maybe this sleeping arrangement helped you as well.”

“Oh no, I’m not uncomfortable that’s…I mean, that’s how it feels,” Richard whispered. His breath made Jared's hair shift, which tickled his own lips.

They still hadn't moved.

“I don’t feel as afraid next to you, you know?”

“ _Oh_ , that’s…” Jared whispered as he curled in even tighter. “Richard, I feel so tiny and safe right now. I can’t describe the feeling.”

“No I, uh, I know what you mean,” Richard murmured. There was a lot of heat, from the sun, from Jared’s body, from Jared’s _words_ , from Richard’s heart exploding a little.

They still hadn’t moved.

Maybe, just maybe, it would be okay to test the waters.

Carefully, he started lightly massaging his fingers through Jared's hair. He was rewarded with a quiet, pleased noise, and the feeling of the other man's body relaxing even further. Emboldened, he moved his other hand from Jared’s hip to underneath his shirt, lightly dragging his fingers up and down the surprisingly hot skin. He felt the slight hitch in Jared's breath, and it made Richard feel dizzy. The hitch turned into a gasp when Richard’s thumb slid underneath the waistband of Jared’s sleep pants.

"Is this okay? Can I…can I touch you like this?"

In response, Jared grabbed the wandering hand and moved it to the front of his pajama pants. Richard groaned and reflexively pushed against what was Jared's very obvious erection.

" _Please_ ,” he gasped, raspy and deeper than Richard had ever heard his voice before.

"Yeah, yes, no problem," he babbled, but he was suddenly still. Even when faced with complete permission he felt nervous, was suddenly aware of what was at stake. He couldn’t move, he had run out of bravery.

But, as always, Jared sensed where he was needed and moved to fill that role.

In a moment Richard was pressed on his back looking into the heartbreakingly earnest face of Jared– _his_ Jared, his Paladin, his new best friend and person who made him dizzy and feel fucking _safe_ –above him.

"Richard, can I–"

"Yes, _yes_ ," he whispered. His last thought was "this guy fucks" before he was kissing Jared fucking Dunn, and he was no longer the DM, never was, was foolish to ever think he was in control. It was Jared, Jared was guiding them, Jared was writing the story, and Richard was dizzy with trust and hope and _want want want, now now, please don't let this ruin everything._


	2. Chapter 2

**Notes for the Chapter:**

> I wanted to do a million things for sex, but then I remembered: no pressure, I can always write more!
> 
> Praise kink-y, if you're into that, but also kind of ridiculously emotional because they are dumb, emotional boys?
> 
> And as a final note, hit me up on Tumblr @glitterdwarf because this tiny fandom is amazing and I love you.

_You’re going to ruin everything_ , Jared’s brain screamed at him. He shivered; this thought felt like a muscle memory, a nervous tic, so well-worn in his brain that it took no more than a slight breeze to push him into it. And, yes, this thought had nearly stopped him countless times before, but it never seemed so scary until now. Now, now that he had Richard— _his_ Richard—underneath him, Richard’s fingers pressed into his back, Richard’s lips against his. And so he did what he had to; Jared slowed and recited his positive affirmations in his mind. But importantly, so importantly, he couldn’t let it show. He had to make sure that Richard was happy and taken care of.

_You are capable._

He pulled his mouth away from Richard’s and let it slide to Richard’s jaw and down his throat, pressing kisses between slow in-out breaths.

 _You are strong_.

He tongued at Richard’s pulse point and sucked while his fingers tangled further into the curly hair that had distracted him for months. He tugged lightly and was rewarded with broken gasps and a leg wrapping around his waist as Richard arched to try and get closer.

 _You are needed_.

Jared huffed a quiet laugh against Richard’s throat, then gave light, slow kisses back up to that adorable, gasping mouth. His own breathing was calm again, all negative thoughts pushed away for now; how could he feel bad when Richard was responding so sweetly?

He released his grip on Richard’s hair and shifted his weight so that he could cup Richard’s cheek. He ran his thumb softly down that cheekbone and smiled as Richard’s body relaxed.

“Shh,” he whispered against Richard’s lips. “We can go slow. We’re kind of still waking up.”

 _You are wanted_.

Richard groaned and tried to press their pelvises closer, eyes fluttering open.

“But Jared, you—you—you _teased_ ,” he stuttered. “I—I just, I want you _so fucking much_.”

And there was that involuntary shiver that happened sometimes; he felt this strong sensation of _burning_ and _want_ travel up his entire body and his eyes fluttered in response. Richard, being so _clever_ and _smart_ caught this. Jared watched through that blissed haze as Richard grinned, getting that look in his eyes like Jared was a programming assignment to suss out, a code to write, an action that would reach its potential with the right touch of his fingers. Richard’s hands moved to pull harder at Jared’s shirt, trying to bring him closer.

“Jared, I _want_ you,” he whispered. “I can’t wait any more.”

Jared’s body nearly fell forward from the shiver this time. He closed his eyes and filed that voice away in case this was his one and only chance to hear it.

“Richard,” he panted. “If it’s okay, I’m going to undress you now, and I’m going to touch you. You can stop me if you feel uncomfortable at any time.”

He felt a puff of air from Richard’s laugh, and then he was pulled down for an amazing kiss. It was soft and lingering, but short, before there were shirts to be taken off and pants to be pushed down. And then suddenly they were bare, skin-to-skin, staring into each other’s eyes.

“Do you have any prophylactics and lubrication?” Jared asked quietly. Richard’s eyes widened and he barked out a surprised laugh.

( _Ruining it_ , Jared’s ghosts hissed in his ear.)

“Yeah, just let me get it,“ Richard said, grinning. They readjusted themselves so that the programmer could get to his knees and reach forward to get into his dresser and rummage.

( _Ruining it_.)

When Richard had straightened up, condom and lube in hand, Jared was already there to hold him in place against the dresser.

 _(Ruining it_.)

“Stop me at any time,” Jared whispered.

 _(“Pull out all the stops, Donald. You can do it,”_ the quiet, anxiety-fighting voice inside told him.)

Jared was on his knees right behind Richard, arms encircling the other man. He ran his hands down Richard’s chest, lightly scratching as he went. He brought them back up and let his fingers lightly graze against the other man’s nipples. That gasp was the unmistakable hint that Richard liked his nipples touched. Richard’s head rolled back to rest against Jared’s shoulder, making it only too easy for Jared to tilt his head to whisper into his ear.

“Good?” Jared asked. He flicked his thumbs against the now-erect nipples. “Good?”

“Yes,” Richard hissed, dropping the condom and lube on the ground. Jared then pinched and rolled his fingers to keep Richard from getting distracted.

“Still good?”

“ _Fuck yes_ ,” Richard gasped. Jared smiled and nuzzled his nose into Richard’s adorable curls. He moved one hand down to take Richard’s dick into his fist. Richard gasped and arched his back to bring his ass in contact with Jared’s erection. A shiver, and Jared impulsively rocked them both forward.

“Jared, Jared, I want you to fuck me,” Richard whispered. Jared felt like he could pass out just from that sentence alone. He was sure that Richard could feel the way Jared’s erection twitched where it was pressed between them, which was a dizzying thought all on its own.

“Have you been penetrated before?”

“Yeah, just not in, well, awhile,” Richard mumbled as he rocked forward into Jared’s fist. “I mean have you, ah, _fuck this is—_ have you fucked a guy before?”

“Yes,” Jared whispered.

_But no one as important as you._

“Oh,” Richard breathed out, hips stilling. “Yeah, I mean, ‘this guy fucks,’ of course you have, probably more than me and, yeah.”

Jared removed his hands from Richard’s body and sat back on his ankles. “Richard, please, look at me.”

Richard shuffled around to face Jared, trying to avoid his gaze. Jared couldn’t see him sad; he reached forward to hold his friend’s hands and brought them to his lips to kiss them. He steeled his voice into the calming one that he used so often with his C.E.O.

“Richard, yes, I’ve slept with people before. Not a lot, but enough to let me know that I can make you feel very good.” He closed his eyes.

( _Going to ruin it._ )

“But honestly, Richard, I haven’t cared about any of them like I care about you. I hope that this admission doesn’t ruin—“

Suddenly Richard was in his arms, around him, kissing him, pressing into him until they were laying down again. It was Jared’s turn to just take and respond, letting out some sounds that would likely embarrass him later.

“You didn’t ruin—Jared,” Richard whispered against his lips between hot, insistent kisses. “Just, just please know that you can’t. You _can’t_ ruin _anything_. You _fix_ things, you fix businesses and you fix _me._ And please, just, I know you want to tell me how that last part is wrong and something about how I don’t need to be fixed but just…would you please just _fuck me already_ and we’ll argue about it later, about who is better and who likes the other more and anything you want, I’ll tell you that you’re good, I’ll praise you for everything because it’s all amazing, I’ll do whatever you want just _please_ _fuck me now_.”

(“ _See? You didn’t ruin anything.”)_

A shiver, an exhale, a grin.

“Yes, anything, yes.”

Things moved quick from there. They were still two men with a lot of lines and angles between them, long and thin limbs that needed to be coordinated. But for the first time in his modest sexual history Jared was just breathing through it all, calm, no longer needing the assurance mentally but able to just enjoy the shock of pleasure every time he was praised.

“Yes, _so good_ ,” Richard gasped wetly when Jared swallowed him down. This became his chant, especially after Richard noticed how it made Jared moan with every single repetition. By the time Richard was stretched and prepared Jared was grasping at the base of his own cock, having to breathe in deep. He knew it was a futile thought that he wanted it to last, not after all of this build-up, but he certainly wanted more than thirty seconds.

Then, he was sliding in, and he was _there_. He was surrounded by Richard everywhere, waist tightly encircled by Richard’s legs, back and shoulders reddened by the pressure and scratches of Richard’s hands and fingers and nails. It was intense, it was _so_ intense, because he could feel his own heart beat in his throat and shoulder where Richard had been biting down to muffle himself, and he could also feel Richard’s heart beat through his fingertips. They were waves rolling together, fluid, unstoppable.

Jared was determined to hold out on his own orgasm until he knew that Richard had been sated. When he pulled back it was only to shift their positions; he wanted to be able to stroke Richard into an orgasm and he wanted to be able to see what his face looked like when it happened. Richard did not disappoint; his flushed chest, neck and face looked so pretty, and only got prettier as Richard came onto his own stomach and chest. Jared stilled his motions to gently stroke Richard through his orgasm, smiling in a way that he was sure looked ridiculous.

“Jared,” Richard panted out. “Jared, don’t stop. You didn’t finish yet.”

“Oh, it’s okay,” Jared started to say, ready to pull out and maybe finish quietly in the bathroom. Instead Richard used—surprising, honestly—strength  to pull him down. He started rolling his hips until Jared picked up the rhythm and resumed fucking into Richard.

“Jared, Jared, please, I need you to come for me,” he insisted before taking Jared’s mouth in a wet, slick kiss. “Come for me, my good boy.”

And then there it was, all the build up and the heat and the pressure and _there_ , he was gone, he was done, he was coming inside Richard fucking Hendriks.

He didn’t pass out, though it was close.

He _did_ , however, apparently let out a loud stream of German curse words that he wasn’t aware of, which amused Richard greatly.

He didn’t leave, and he didn’t get pushed out, which is what he thought would happen. He was sure that Richard was this thing that he could touch once, but no more.

He did, instead, get taken care of, which was a new and awe-inspiring thing to experience. Richard took care of the condom, took care of wiping the both of them down, and then covered Jared’s body with a blanket when it became obvious that he was going to fall asleep again. They then laid together in much the same position they had been the previous night.

He also pretended to be more tired than he was when Richard was starting to pull away and leave. He should have let him go, of course; there was a lot to get done and a lot to work on, and they had already spent a lot of the morning away from Pied Piper work. But instead he used the skill he learned long ago, the one where he controlled his breathing to make it seem like he was asleep.

After all, if he was asleep, he couldn’t be blamed for tightening around Richard, like he had last night. He then he certainly couldn’t be blamed for what happened next, which was Richard whispering “I love you,” and the fluttering in his own chest.

He was so tiny, so safe in Richard’s arms. The feeling was _indescribable._

Honestly, he would have to be careful with how he wrote about it in the blog.


End file.
